Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

Participants

Reaction Steps

Diethyl benzylmalonate is reduced with lithium aluminium hydride to give 2-benzylpropane-1,3-diol (m.p. 64°-65° C.) and esterified with an equimolar amount of benzenesulphochloride in anhydrous pyridine to give 2-benzylpropane-1,3-diol monobenzenesulphonate (oily substance). Reaction thereof with the sodium salt of hexadecanethiol in ethanol gives the desired 2-benzyl-3-hexadecylthiopropan-1-ol (wax-like compound).

Provenance & Evidence